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With the series being a Long Runner, it’s no surprise that a timeless show like The Simpsons can have many hilarious moments through its time. Nowadays, however, some of the past episodes aren't so funny anymore when viewed today.

  • One of the last scenes of "New Kids on the Blecch" depicts the MAD building being blown up after (almost) publishing an unflattering satire of Bart, Milhouse, Nelson, and Ralph. This episode aired seven months before 9/11, and that scene ended up getting cut in some syndicated broadcasts for a while as a result. Also in January 2015, the headquarters of French satirical magazine Charlie Hebdo were attacked by terrorists for publishing a satirical image relating to Islam.
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  • In Season 5's "$pringfield", which aired on December 16, 1993, two No Celebrities Were Harmed versions of Siegfried & Roy perform an act with a white tiger riding a unicycle. The act goes horribly wrong when the tiger attacks both illusionists due to the mistreatment that she has suffered. A decade later, a white tiger actually did attack Roy during one of their shows. The DVD commentary declared it the "greatest prediction ever made by The Simpsons," though the writers also pointed out that the tiger attack was bound to happen sooner or later, considering how she was treated.
  • In the Season 10 episode "Sunday, Cruddy Sunday" (which aired after Super Bowl XXXIII on January 31, 1999), Nelson asks if the postman has ever gone on a rampage and killed people. The postman remarks that the disgruntled mailman stereotype is a thing of the past. Principal Skinner then replies, "I'm glad I work in an elementary school!". This episode premiered when the trend of kids going ballistic and opening fire at their schools was a hot topic, and with one of the most infamous school shootings of all — Columbine — taking place just a few months after it aired, the joke's darkness gets blacker and a lot more tasteless. The Sandy Hook Elementary School shooting on December 14, 2012 and seemingly one a week in recent years would make this line even more tasteless.
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  • There's a scene in "Marge vs. Singles, Seniors, Childless Couples and Teens, and Gays" where Bart wants to watch a TV show where Steve Irwin gets mauled to death by an animal. On September 4, 2006, Irwin died when a stingray pierced his heart.
  • The series' monkey/ape references can be considered this for the following reasons:
    • A lot of the earlier episodes had verbal jokes and sight gags depicting Homer as a monkey. In addition, he was often called a "big ape" due to his crass behavior and informed ugliness. These stop being funny with "The Color Yellow", which reveals that one of Homer's ancestors was a black slave.note 
    • There's the line in "Weekend at Burnsie's" when Homer, who's been smoking medicinal marijuana after getting pecked in the eyes by crows, states that he can go up to The President and "... blow smoke in his stupid monkey face, and he'd be sitting there groovin on it!" This line would be considered horrifically racist during the presidency of Barack Obama.note 
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    • Homer sees a movie called Hail to the Chimp at the drive-in theater in the Season 9 episode "Dumbbell Indemnity." This scene would become very racist in the Obama era.
  • The Season 5 episode "Lisa vs. Malibu Stacy" has a scene where Grandpa admits that stole Andy Griffith's pills while the latter, who's in character as Matlock, is in an ambulance next to him being rushed to the hospital for a heart condition. This became significantly less funny after Griffith's death on July 3, 2012. Furthermore, it was determined that his death was caused by a heart attack.
  • "Lisa's Date with Density":
    • Lisa asks Milhouse to send Nelson a love note from her, but Nelson is led to think the note's from Milhouse himself. Cut to Milhouse being led away in a stretcher to an ambulance, with the paramedics telling Lisa that Milhouse can't hear her.note  It really stops being funny after the highly publicized rash of suicides and murders from bullying, especially anti-gay bullying. The setup of the scene is horrifyingly very similar to the murder of Lawrence King in 2008.
    • Nelson's version of "Joy to the World" (where a teacher suffers a gruesome death by the kids' hands) becomes much less funny to UK viewers in light of a teacher being stabbed to death by a student during a lesson in April 2014.
  • During the end credits of the clip show "All Singing, All Dancing", Snake fires his first gunshots when Phil Hartman's name comes up saying, "Yo! I told you to stop the music, dudes. I'm serious!". Four months after it first aired, Hartman was shot to death by his wife in a murder-suicide.
  • "A Totally Fun Thing That Bart Will Never Do Again" centers on Bart sabotaging a cruise ship so his cruise vacation can last forever, which leads to disaster. In February 2013, a similar situation happened to Carnival Cruise Line's Triumph.
  • In the Season 7 clip show episode "The Simpsons 138th Episode Spectacular", the original three Simpsons showrunners-cum-creators are Matt Groening (depicted as a gun-crazy redneck), James L. Brooks (depicted as being very fat, very rich, and the winner of several awards), and Sam Simon (depicted as a frail expy of Howard Hughes in his later years). Simon was diagnosed with terminal cancer in early 2013 and died two years later.
  • In "A Star Is Burns", the crossover episode with The Critic that Matt Groening hated, there is a scene from Rainier Wolfcastle's horrible stand-up comedy movie where his Woody Allen "impression" is just Wolfcastle saying, "I'm a neurotic nerd who likes to sleep with little girls." Back then, it was a Take That! at him marrying his stepdaughter, Soon-Yi. Things got worse, when in October 2013, his adopted daughter, Dylan, alleged he sexually abused her twenty years earlier.
  • The "Treehouse of Horror XII" segment "Hex and the City" features a helicopter crashing into Moe's Tavern, killing Lenny and Carl. Twelve years later, a police helicopter did just that in Scotland.
  • In "Treehouse of Horror IX" there is the mention that one of the series also produced by World's Deadliest Executions was titled Secrets of National Security Revealed. In 2013, Edward Snowden stepped down from the NSA after outing himself as the man who revealed the more controversial methods used to gain information at the NSA.
  • In "Brother's Little Helper", then-single season home run record holder Mark McGuire shows up when Major League Baseball was found to be using spy satellites to collect marketing data on Springfielders. His offer to tell everyone the "terrifying truth" or hit a few dingers is now incredibly awkward seeing as how he and other major hitters of that era were using various steroids to improve their performance. It's also poignant seeing as how, at the time, many fans were in fact content to see him "hit a few dingers".
  • A scene in "Lisa the Beauty Queen", normally cut out for syndication, shows Otto operating a faulty rocket ride and after causing it to spin faster at Bart's request, one of the rockets falls off and crashes into the school. 20 years later, Australia was plunged with two fatal accidents with theme park rides. In 2014, an eight-year-old Malaysian girl was thrown off a ride and killed at the Royal Adelaide Show. Two years later, four people were killed in a collision on the Thunder River Rapids Ride at Dreamworld. Poor safety was blamed for both incidents.
  • In "The Old Man and the "C" Student", which originally aired on April 25, 1999, there's a reference to Russia's then recent currency crisis with a Russian Olympic Committee representative panicking as the ruble collapses to 1000 to the dollar in just a few minutes. Come 2014 where the ruble suffered a collapse just as bad as the one in the late '90s due to falling oil prices.
  • A scene in the 1999 episode "Monty Can't Buy Me Love" depicting billionaire Arthur Fortune proudly knocking out a retired Muhammad Ali. This was already in rather bad taste, given that Ali was by then quite significantly crippled by Parkinson's disease.note  The gag became even more uncomfortable in the years that followed as Ali became ever-more frail before eventually dying from septic shock on June 3, 2016.
  • In "I've Grown A Costume on Your Face" from "Treehouse of Horror XVI", Chief Wiggum becoming 'Jared from the Subway ads' and referring to himself (Jared) as 'sexually ambiguous' is a lot more uncomfortable since Jared Fogle's arrest for child porn possession.
  • In "Ice Cream of Margie (with the Light Blue Hair)", Homer forces a lactose-intolerant boy to eat an ice-cream bar, causing him to collapse as he tells Homer to call the number on his bracelet. In 2017, an allergic toddler died when his preschool allegedly forced him to eat a grilled cheese sandwich.
  • In "Mayored to the Mob", Mayor Quimby tells Mark Hamill to attack the angry convention attendees with his lightsaber, to which Hamill replies “What, and break it!? Y'know, George Lucas makes me pay for these!” This is what ends up happening to Luke’s original lightsaber in "The Last Jedi".
  • In "Behind The Laughter" the episode ends with a teaser for a "future" episode of Behind the Laughter featuring Huckleberry Hound admitting he is a closeted homosexual. Come 2018, the DC comic/graphic novel "Exit, Stage Left!: The Snagglepuss Chronicles" portrays Huckleberry Hound as a troubled gay man, and this is Played for Drama up until he hangs himself after being arrested during an anti-gay raid.
    • Homer comments at the end: "this is the last season". Homer's European Spanish voice actor, Carlos Revilla, died suddenly not long after dubbing the episode.
  • "Mr. Lisa's Opus" has Bart making a crack that Lisa has "a voice that would make a rhino want to shove its horn in a socket", and then another that Homer is a hippo after Lisa responds to him that rhinos are extinct. Come March 20, 2018 when the last male northern white rhinoceros had died, making the subspecies functionally extinct.
  • In "Viva Ned Flanders", the people running away from the dust cloud after Mr. Burns' casino gets demolished, looks eerily similar to the cloud caused by the collapse of the Twin Towers, two years after the episode was aired.
  • In "Round Springfield" Krusty has a new sidekick (Mrs. No Means No) who is court ordered after a sexual harassment suit, which he blames on his addiction to Percodan. In 2018, the reboot of Roseanne was retooled into The Conners after Roseanne Barr made racist Twitter posts which she blamed on being under the influence of Ambien.
  • As if Mario Batali's advice to Homer to cook his remaining body parts as ingredients sold at Chez Homer and several other restaurants across Springfield in the "Mmm... Homer" segment of Treehouse of Horror XXVIII wasn't bad enough, the sexual allegations against Batali a few weeks after the episode aired is now making his appearance not just creepy, but also as downright uncomfortable as Homer's Autocannibalism.
  • "The Last Temptation of Homer" had the Department of Labor raid the Power Plant. One of their accusations involved harboring a Brazilian soccer team and forcing them to work in the reactor core. His response? "That plane crashed on my property!" In 2016, a plane carrying the Brazilian soccer team Chapecoense crashed in Colombia en route to a tournament final, killing most of the players on board.
  • "The Fool Monty" had Dick Cheney asking Smithersnote  if there had been any terrorist incidents on American soil during the day (being visibly disappointed by the fact there were none), a question that in 2010 would make the former VP look like a paranoid loony. The following years saw a surge of "homegrown terrorism" in the West, primarily shootings in the case of the U.S., making the question seem far less far-fetched.
  • In "The Twisted World of Marge Simpson", at a Springfield Isotopes game, Springfielders are so angry at Mr. Burns "winning" the raffle that they start throwing Marge's pretzels at him, littering the field and hurting Whitey Ford. During a 2001 NFL game with the Jacksonville Jaguars vs. the Cleveland Browns, the NFL referees controversially overturned a potentially game-winning play for Cleveland, making Cleveland fans so angry that they threw bottles and other objects at them, leading to the game being dubbed "Bottlegate".
  • In "The Italian Bob", the family go to Italy and Homer gets in trouble for seemingly impersonating Benito Mussolini, which he explains was actually him "doing Donald Trump". We'll just leave it at that.
  • In "Bart Gets Famous" Bart has an Imagine Spot 40 years into the future guest-starring on Match Game with other celebrities including Loni Anderson, Billy Crystal and Farrah Fawcett, in real life Farrah Fawcett succumbed from anal cancer on June 25, 2009.
  • An example that happened quickly after it came out: in "Team Homer" Homer is shown having stolen the Academy Award for Best Supporting Actor given to Dr. Haing S. Ngor for The Killing Fields. Only a month after it first aired, Dr. Ngor was murdered, which would make viewers today think Homer killed him for it. In syndication and on the season seven DVD set, the scene was changed to show the Oscar being the one given to Don Ameche for Cocoon, who had died a few years earlier, but of natural causes.
  • The episode "Walking Big & Tall" had Bart and Lisa call back to the earlier episode "Stark Raving Dad", with the children remarking that in hindsight it was pretty careless of their parents to leave Bart with Leon Kompowsky (who was voiced by Michael Jackson credited under the pseudonym John Jay Smith) when he was confirmed to be mentally ill. What was initially nothing more than playful ribbing at Homer and Marge's borderline moments of parental negligence becomes even more startling in light of the decision to pull "Stark Raving Dad" from circulation after the documentary Leaving Neverland re-opened the child molestation allegations directed towards Jackson and Al Jean voicing his suspicions that Michael Jackson agreed to guest star on the episode solely to groom more children to molest.
  • In "Bart Vs. Australia", Bart jokes "I hear a dingo eating your baby", a reference to the memetic line from Evil Angels, based on the real life disappearance of Azaria Chamberlain. However, evidence has since shown that a dingo did in fact eat the two-month-old child.
  • "Saturdays of Thunder" has Homer reading a parenting book written by Bill Cosby and reads out loud "Cosby's First Law of Intergenerational Perversity". With all the accusations and charges of sexual assault in the mid 2010's against younger women it's suddenly a lot less comfortable to hear about Cosby's views on "intergenerational perversity", actual context be damnednote .
  • In "Grift of the Magi", guest star Gary Coleman is portrayed as a Cloud Cuckoo Lander, which becomes quite unsettling considering the years before his death in 2010.
  • The sub-plot of 2009's "The Good, the Sad and the Drugly" had Lisa fretting after reading about a potential collapse of civilization by 2059. About a decade after this episode aired, fears about society falling apart in the near future became disturbingly commonplace, with an Australian report indicating that the human race might become extinct by 2050 in the best of cases, a forecast backed by a similar UN study.
  • In "Homer Loves Flanders", Homer plays a "Rappin' Ronnie Reagan" tape which consists of President Reagan repeating the word "Well?" over and over, much to the others' annoyance. Five months after the episode aired, the real Ronald Reagan went public with his Alzheimer's diagnosis.

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